


Trust

by TheRoguelock



Category: Critical Role (Web Series)
Genre: Caleb Widogast Deserves Nice Things, F/M, POV Caleb Widogast, Pining Caleb Widogast, Sweet Jester Lavorre, Widojest Week
Language: English
Status: Completed
Published: 2020-07-08
Updated: 2020-07-08
Packaged: 2021-03-04 20:00:57
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,067
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25142038
Author URL: https://archiveofourown.org/users/TheRoguelock/pseuds/TheRoguelock
Summary: Before embarking on an important mission, Jester and Caleb rely on each other to be honest with their opinions, even if they don't know it...
Relationships: Jester Lavorre/Caleb Widogast
Kudos: 35
Collections: Widojest Week 2020





	Trust

**Author's Note:**

> I had planned for this to be a continuation from the Dance fic (“Ruby, Sapphire and Amber”), but a certain piece of art caught my eye and changed my plans only slightly, so this is something different. Still occurs after episode 97.

As Caleb set about removing his coat and belt, he could not help but wonder how it had come to this.

They’d agreed to look into the business dealings of a Nicodraninan noble and his wife, and had gone to great lengths to arrange a meeting with them, forging a letter that would allow them to pass as a foreign dignitary. They had been surprisingly open to the idea of having guests, but seemed to insist on having two people join them for dinner.

The Nein debated for what seemed like an hour on who should go: it would be important to have two people who knew how to behave in a manner that nobility would be accustomed to. For that matter, Yasha and Caduceus were eliminated, Clay not really grasping the nuances and intricacies of dining etiquette, and Yasha unable to fathom why someone would “make a big deal about eating”. Nott was out as her stealth and finesse was key to the operation.

This left Beau, Fjord, Caleb, and Jester. Fjord recused himself from any talks of having him attend, joking that he’d never bothered to learn the difference between all the spoons that were used in such fancy settings. Beau’s upbringing lent her some experience in high-society, but she’d seemed uncomfortable with the idea and offered to back up Nott instead.

Caleb, of course, had been taught how to mingle with those of the upper crust in his younger years, and acknowledged that while a little rusty, he could fake enough proficiency to make himself appear highborn.

Jester had had little application of any social skills in interacting with the upper class (Lord Sharpe didn’t count, as he was a tool). But she appeared eager to learn, and suggested that her mother help them to review or relearn anything they would need.

Marion agreed to teach them, and she taught both for a few hours, Caleb taking care to memorize all the rules she laid before him and helping to keep Jester interested when he noticed her eyes start to glaze over.

Marion suggested they take a break for an hour or two, which caused Jester to smile that same way she did when she had been planning something for hours.

With no warning, she grabbed Caleb’s hand and dragged him out of the Château, ignoring his questions of where they were going until they were standing in front of what appeared to be a high-end clothing boutique.

“Jester,” Caleb began, “We already have very nice clothes that you got for us before. Do we really need to get more?”

Jester gave Caleb a jokingly hurt look. “Cayyyleb…We can’t wear those. Those were for a party.” She grabbed Caleb again and pulled him through the double doors of the building, a bell tinkling softly as they entered.

“We need fancy dinner clothes. That’s a totally different thing.”

Caleb shook his head, a smile on his face despite the ridiculousness of her logic. “Very well. I trust you to find me something exquisite yet again Ms. Lavorre.”

Jester clapped her hands together in delight, turning to talk briefly to the receptionist who had stepped forward to assist them, before running off and disappearing into the store.

Taking a moment to inquire where the changing area would be, Caleb was directed towards a series of benches in front of a set of several mirrors arranged in a semi-circle pattern, designed to allow one to see their clothing from every available angle.

He waited for about 10 minutes before Jester returned, her arms laden with different outfits, shoes, and various accessories. She dropped one armful on one bench and the other on a different, taking a minute to sort each of the outfits from the others.

She whirled on him, eyes almost sparkling with manic energy and a wide smile on her face. “Alright, so you sit there and tell me what you think Caleb.”

Caleb seemed confused for a moment, but nodded. Jester beamed at him and gathered up almost all of the outfits she had laid out, disappearing behind the mirrors.

What followed next was 30 minutes of a whirlwind of clothing. Jester appeared before him in several different ensembles: a dress with a skirt even poofier than the one she had worn at the Marquis’ estate, and another similar to the one her mother had worn that same night. Half a dozen dresses and evening gowns appeared before Caleb, Jester seeming to look for something in his eyes for a minute before moving back behind the mirrors to change again.

To her credit, Caleb thought, she did not look bad in any of them, though he figured he might be somewhat biased. She appeared uncomfortable in several of the outfits though, her face a grimace as she tried to smile expectantly at him. He wondered if his concern was registering as disapproval for her choices, but had no time to think on that as she called from behind the mirror.

“Okay,” came her voice, more nervous than he was accustomed to hearing. “This is the last one.”

As she stepped from behind the mirrors, Caleb could practically feel himself inhale. The dress she was wearing started as a bright pink around her shoulders, dipping into a V that highlighted her diamond dust tattoo. The color faded slowly as it reached the bottom, becoming nearly white at the very bottom of the hem, which he noticed stopped just around her ankles. The dress was fashioned in such a way that it appeared to be tied above her left hip, the bow remaining dangling a few inches below where it was knotted. He noticed that she appeared to be wearing some kind of light pink shorts under the dress, but reasoned something so simple couldn’t possibly look so lovely. Sheer, pink, almost see-through fabric was gathered around the shoulders of the dress, tumbling down her arms to about the elbows. He looked further down and noticed the sandals she was wearing, which appeared to be rose-gold in color. There was a heel at the back, and straps wrapping all the way around her legs up to mid-thigh, split down the middle of her leg by one long, singular strap. She had various bangles around her wrists, and hoop earrings in her ears, faux jewelry that the shop allowed her to borrow.

Jester reached up to tuck a strand of hair behind her ear, which hung loose now except for one bun at the back of her head, the rest tumbling down past her shoulders. She looked up at Caleb, who not quite noticing a look of concern, almost fear in her eyes as she looked for his opinion.

Caleb struggled to talk for what he guessed was half a minute, his mouth opening and closing like a goldfish.

“Ja,” he finally managed to get out. “I… I think that looks good on you.”

Jester beamed at him as he said that, stretching her arms out to give a quick twirl, looking at her reflection in the various mirrors before turning back to Caleb. “I like it too. It’s definitely easier to move in then some of those other ones.”

Caleb could only nod as she stepped back behind the mirrors. He pressed his hand to his chest and swallowed, feeling his heart racing in his chest.

Jester walked back out from behind the mirrors, dress draped over her arm, smoothing her hair back into its original style.

She set the dress delicately on an empty bench, gathering up the remaining outfits and handing them to an employee that she waved over.

She looked expectantly at Caleb, who had managed now to get his breathing under control. “I only found one outfit for you, but I think you’ll really like it.”

She handed him a folded mound of cloth, which he noticed was a dark shade of purple. He eyed her for a moment, an eager smile on her face as she gauged his interest. He returned the smile and took the clothes from her, surprised when she handed him a pair of shoes as well. He stepped behind the mirrors to find a small room, door slightly ajar from where Jester had exited. He stepped inside and placed the clothing upon a hook.

As he began to remove his clothing, Caleb shook his head at his current predicament. He couldn’t believe that he had allowed Jester to convince him they needed more clothing. He didn’t really see the point of getting himself anything new, though the experience of seeing her in that dress was certainly a convincing argument after the fact. He shook the thoughts from his head and finished putting on the garments Jester had chosen for him before stepping outside.

Jester was waiting on one of the benches as he stepped around, humming quietly to herself. She turned to look at him, a smile on her face that quickly turned into shock.

Worried that he looked unbecoming, Caleb turned to look at himself in the various mirrors. The outfit that Jester had chosen for him was indeed a deep, rich purple, mostly uniform in color. He wore a high-collared, single-breasted jacket that slightly overlapped and buttoned slightly to the right of the center of his torso. This was covered by a tiered cape, with one layer starting at the collar of his jacket and falling to about the middle of his chest, while the second, bottom layer extended all the way from his collar to the hem of his pants. The lining of the cape seemed to be a somewhat lighter shade of violet. The cape was held around his neck by a pair of thin golden chains, and the edges of his cape and the bottom cuffs of his pants were dusted with what appeared to be gold. A set of light gray shoes and a set of gloves the same color as his jacket completed the ensemble. 

He turned back to Jester, a look of concern on his face. “Does it look that bad?” he joked.

Jester seemed stunned for a moment before blinking rapidly and shaking her head side to side. “No, no, no. It’s just… It looked good when I picked it out, but I didn’t expect it look so good when you put it on.”

Caleb looked off to the side at that, reaching up to scratch at the side of his face with a finger. He noticed the blush splashed across his face out of the corner of his eye, reflected in one of the mirrors.

He looked back up to find Jester a foot from him now, surprising him.

“Sorry,” she apologized. He noticed a light blush across her face as well.

“I just,” he noticed she had something in her hand, which he failed to identify as she reached behind his head. “I think this will look good with your outfit.”

He said nothing as she felt her pull at his hair for a few seconds. He was focused on her face, a few inches from his now. He watched as she seemed focused on something, chuckling slightly as her tongue stuck up from between her lips.

That earned a small pout from her, but she finished her work and stepped back, looking pleased with herself. Caleb turned to look at himself in the mirror, noticing that she had put his hair up into a ponytail, but had gently pulled out the end somewhat to give it more volume.

“Perfect,” Jester said from behind him. He turned to see her gathering her dress before smiling at him. “Now we’re all ready.”

Caleb paused to look at her for a moment before returning the smile, stepping back around the mirrors to change back into his normal attire.

They made their way out of the shop, balking somewhat at the price, but each agreeing that it was well worth it.

As they approached the Lavish Château, Caleb felt Jester bump into him. He looked down at her, his eyes drawn to her beaming smile.

“You see? It’s nice to get new clothes sometimes, huh?”

Caleb thought back to how she looked as she stepped around the corner, how she’d smiled as she twirled in front of the mirrors.

He smiled softly down at her before turning to look back towards the Château.

“Ja. I suppose it is.”

**Author's Note:**

> Alright. That’s another one down.
> 
> This one also could have gone longer, but I’ll have a proper sequel for this later (I promise this time).
> 
> And for reference, here’s the art in question that caused me to change my plans: https://twitter.com/cassartsalot/status/1280368855609737216. Go show the artist some love!


End file.
